CN104497579A - One-component room temperature vulcanized organic silicon rubber with high adhesion and preparation method thereof - Google Patents
One-component room temperature vulcanized organic silicon rubber with high adhesion and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a one-component room temperature vulcanized organic silicon rubber with high adhesion and a preparation method thereof. The one-component room temperature vulcanized organic silicon rubber with high adhesion is prepared from the following components in parts by weight: 50-150 parts of hydroxyl-terminated silicone rubber, 50-150 parts of alkoxy-terminated maleopimaric acid modified polysiloxane resin, 10-20 parts of a filler, 2-10 parts of a crosslinking agent and 0.1-0.5 part of a catalyst. The one-component room temperature vulcanized organic silicon rubber with high adhesion overcomes the disadvantages in the prior art of poor adhesion of substrates including silicon increasing rubbers, metals and plastics, is outstanding in mechanical properties and has important environmental protection value and very wide application prospect by adopting green and renewable maleopimaric acid which is a derivative of natural rosin as the raw material.
Description
Technical field
The invention belongs to Material Field, be specifically related to a kind of single-component high adhesion room temperature vulcanization organosilicon rubber and preparation method thereof.
Background technology
Single-component room-temperature-vulsilicone silicone rubber RTV-1 has excellent resistance to chemical attack, high-low temperature resistant, weather-proof, moisture-proof and the performance such as ventilative, and it is easy to use, without the need to hot setting, be thus widely used in the sealing of high temperature resistant element and bonding, become the staple product in silicone industry.But the natural characteristics by organosilicon material limits, the cohesive strength of organosilicon RTV-1 is low, weak with the adhesive power of the base material such as plastics and metal, and these shortcomings all strongly limit the application of organosilicon RTV product.
For solving the problem, usually adopt the method for adding viscosity increaser, but currently used binding agent is the viscosity increaser containing strong polar group, is petroleum-based compound, all derives from petrochemical complex, is Nonrenewable resources.Along with the day by day exhausted of petroleum resources and environmental requirement progressively improve, adopt reproducible natural resource to solve the thickening problem of current organosilicon RTV, there is very important Development volue.
Summary of the invention
Technical problem solved by the invention is to provide a kind of single-component high adhesion room temperature vulcanization organosilicon rubber and preparation method thereof, to overcome in prior art single-component room-temperature-vulsilicone silicone rubber and the defect such as adhesion is weak, poor mechanical property, raw material are non-renewable.
For solving the problems of the technologies described above, the technical solution adopted in the present invention is as follows:
A kind of single-component high adhesion room temperature vulcanization organosilicon rubber, its raw material comprises following component:
Hydroxy-terminated silicone rubbre: 50 ~ 150 parts;
Alkoxy end-capped maleopimaric acid modified polysiloxane resin: 50 ~ 150 parts;
Filler: 10 ~ 20 parts;
Linking agent: 2 ~ 10 parts;
Catalyzer: 0.1 ~ 0.5 part;
Above-mentioned number is mass fraction.
Above-mentioned single-component high adhesion room temperature vulcanization organosilicon rubber excellent in mechanical performance, have very strong adhesive power, and alkoxy end-capped maleopimaric acid modified polysiloxane resin is renewable raw materials, meets Sustainable development requirement with the base material such as plastics and metal.
Amount of filler of the present invention is crossed conference and is caused Rubber processing difficulty, and after too low then sulfuration, mechanical strength of silicone rubber is too low.
Dosage of crosslinking agent is too high or too low all can cause rubber product sulfuration incomplete, thus affects the use properties of product.
Catalyst levels is too high or too low all can cause rubber product sulfuration too fast or too low, thus affects the use properties of product.
The structure of above-mentioned alkoxy end-capped maleopimaric acid modified polysiloxane resin is:
Wherein,
R
1for methoxy or ethoxy;
R
2and R
3for the straight-chain alkyl of carbon number 1 ~ 3;
The value of a is 0,1 or 2;
The span of m and n is, and meets simultaneously: 0.5≤n/ (m+n)≤0.02;
X to be carbon number be 2 ~ 10 alkylidene group, i.e.-C
bh
2b-1-, 10≤b≤2.
Adhesion property and the mechanical property of organo-silicone rubber can be ensured so further.
Arbitrary Digit in all desirable 1 ~ 100 scope of above-mentioned m and n such as, can be decimal or integer, and preferably, the span of m is the span of 1-10, n is 0.1-1; More preferably, the span of m is the span of 4-7, n is 0.5-0.5.
When the value of n/ (m+n) is too high, material viscosity can be caused excessive, mixing difficulty; When the value of n/ (m+n) is too low, can not get a desired effect.
The range of viscosities of described hydroxy-terminated silicone rubbre is 10 ~ 100PaS.Adhesion property and the mechanical property of organo-silicone rubber can be ensured so further.
Described filler is vapor phase process or precipitated silica or through trimethyl silicane surface-treated thermal silica.The synergistic effect between filler and other each component can be promoted so further, and can not impact rubber mechanical property.
The application preferably adopts through trimethyl silicane surface-treated thermal silica, because it not only has good reinforcing effect, and silicone rubber formulations component viscosity can not be caused sharply to raise and cause processing difficulties.
Linking agent is the mixture of one or more any proportionings in dealcoholizing-type linking agent, de-oxime type linking agent or deacetone linking agent.The mechanical property of gained rubber can be ensured so further.
Dealcoholizing-type linking agent is the mixture of one or more any proportionings in methyltrimethoxy silane, vinyltrimethoxy silane, methyl silicate, tetraethoxy or positive silicic acid propyl ester;
De-oxime type linking agent is the mixture of one or more any proportionings in methyl tributanoximo silane, vinyl tributyl ketoximyl silane or phenyl tributanoximo silane;
Deacetone linking agent is the mixture of any one or two kinds in methyl three iso-propenyloxysilane, vinyltriisopropenyloxysilane or phenyl three iso-propenyloxysilane and above any proportioning.The synergistic effect between each component can be promoted so further.
Catalyzer is organic tin catalyzer or organic titanium class catalyzer.Adhesion property and the mechanical property of gained rubber can be ensured so further.
Organic tin catalyzer is the mixture of one or both and above proportioning arbitrarily in dibutyl tin dilaurate, dibutyl tin acetate, stannous octoate or stannous iso caprylate;
Organic titanium class catalyst Ti isopropyl propionate, tetrabutyl titanate or ethylacetoacetate titanium to boil together in thing the mixture of one or both and above proportioning arbitrarily.Further can ensure adhesion property and the mechanical property of gained rubber like this.
Above-mentioned single-component high adhesion room temperature vulcanization organosilicon rubber, the preparation method of alkoxy end-capped maleopimaric acid modified polysiloxane resin used, comprises the following steps that order connects:
Step 1: by octamethylcyclotetrasiloxane D
4100 parts, containing primary amine groups-NH
2alkoxy silane coupling agent hydrolyzate 1 ~ 200 part, end-capping reagent organoalkoxysilane 2 ~ 100 parts and Tetramethylammonium hydroxide mixing, insulation reaction is stirred 4 ± 0.2 hours at 100 ± 5 DEG C, wherein, the quality of Tetramethylammonium hydroxide accounts for reactant total mass 0.1%, and described number is mass fraction;
Step 2: add maleopimaric acid powder in the material of step 1 products therefrom, and be warming up to 150 ± 5 DEG C gradually in 4 ± 0.2 hours, reaction terminates, wherein, maleopimaric acid with containing primary amine groups-NH
2alkoxy silane coupling agent hydrolyzate mole dosage equal;
Step 3: after step 2 reaction terminates, reaction system is warming up to 180 ± 5 DEG C gradually, and vacuum takes off low-boiling-point substance 2 ± 0.2 hours, and the state of obtaining is the alkoxy end-capped maleopimaric acid modified polysiloxane resin of light brown homogeneous phase transparent thick liquid.
In above-mentioned steps 1, the quality of Tetramethylammonium hydroxide accounts for 0.1% of reactant total mass, and middle reactant total mass refers to the total mass of reactant in step 1.
Preferably, in step 1, containing primary amine groups-NH
2alkoxy silane coupling agent hydrolyzate mass fraction be 5-15 part, end-capping reagent alkoxyl silicone mass fraction be 10-20 part.
Maleopimaric acid is the Diels – Alder adduct of natural rosin and maleic anhydride.Natural rosin, belongs to renewable resources, abundance and cheap, has the advantages such as anticorrosion, moistureproof, insulation, bonding, is widely used in the fields such as papermaking, ink and rubber.Maleopimaric acid is utilized to improve the adhesive power of existing organosilicon RTV product, for slowing down energy dilemma and environment protection has very important realistic meaning.But because maleopimaric acid can not mix with organosilicon, not yet have report it to be applied to the thickening of silicone based tackiness agent so far, maleopimaric acid is then successfully applied in single-component high adhesion room temperature vulcanization organosilicon rubber by above-mentioned means by the application.
Described containing primary amine groups-NH
2alkoxy silane coupling agent hydrolyzate, can be formed by the hydrolysis of the amino silicane coupling agent that is easy to get in industry and drying, there is following structure:
Wherein,
X can be-C
bh
2b-1-, 10≤b≤2.
The amino silicane coupling agent be easy to get in described industry, can choose gamma-amino hydroxypropyl methyl diethoxy silane.
The functionality of described organoalkoxysilane is at least 2, can choose dimethyldimethoxysil,ne, the polyfunctionality organoalkoxysilanes such as methyltrimethoxy silane.
Take dimethyldimethoxysil,ne as raw material, the preparation method of methoxy group maleopimaric acid modification methyl silicone resins is as shown below:
The preparation method of above-mentioned single-component high adhesion room temperature vulcanization organosilicon rubber, comprises the following steps that order connects:
A, hydroxy-terminated silicone rubbre, alkoxy end-capped maleopimaric acid modified polysiloxane resin and filler added in vacuum planetary mixer and carries out dewatering in the temperature range of 50 ~ 100 DEG C blended 1 ~ 4 hour;
After B, blended end, be cooled to room temperature, add linking agent and catalyzer, be uniformly mixed;
C, carry out packing under nitrogen protection, to obtain final product.
The NM technology of the present invention is all with reference to prior art.
Single-component high adhesion room temperature vulcanization organosilicon rubber of the present invention overcomes in prior art the shortcoming increasing silicon rubber and the base material such as metal and plastics poor adhesive force, there is outstanding mechanical property, and the derivative maleopimaric acid adopting green reproducible natural rosin is raw material, there is the important value of environmental protection and very wide application prospect; And preparation is simple, environmental protection.
Accompanying drawing explanation
Fig. 1 is the hydrogen spectrogram of embodiment 1 gained methoxy group maleopimaric acid modification methyl silicone resins.
Embodiment
In order to understand the present invention better, illustrate content of the present invention further below in conjunction with embodiment, but content of the present invention is not only confined to the following examples.
Embodiment 1
Methoxy group maleopimaric acid modification methyl silicone resins (MO-MPA-PDMS), the wherein preparation of m=5.8, n=0.33:
1000g amine hydroxypropyl methyl diethoxy silane is added reactor, slowly adds isopyknic water, stirring reaction 2 hours; Heat up and keep reaction volume to be reflux state; After 2 hours, carry out negative pressure to reaction system and take off low process of boiling, obtain the hydrolyzate HAPMS of 600g colourless transparent liquid gamma-amino hydroxypropyl methyl diethoxy silane, its structure is as shown below:
Add 200g octamethylcyclotetrasiloxane, 18g HAPMS, 28g dimethyldimethoxysil,ne and Tetramethylammonium hydroxide powder (Tetramethylammonium hydroxide quality accounts for 0.1% of total reactant quality) in a kettle. and add four-hole boiling flask, at 100 DEG C, stir insulation reaction 4 hours; Add 39g maleopimaric acid powder, and be warming up to 150 DEG C gradually in 4 hours, reaction terminates; After reaction terminates, reaction system is warming up to 180 DEG C gradually, and vacuum takes off low boiling 2 hours, finally obtains light brown homogeneous phase transparent thick liquid 240g, collects product under nitrogen protection, for subsequent use.Products therefrom MO-MPA-PDMS's
1hNMR spectrogram is illustrated in fig. 1 shown below:
As shown in Figure 1, except the Si-CH of common silicone resin
3outside the chemical shift peak of (0.5 ~ 3.0ppm), also there is following characteristic chemical shifts peak in methoxy group maleopimaric acid modification methyl silicone resins (MO-MPA-PDMS):
The proton uptake peak on CH=C in horse pimaric acid structure has been there is near 5.4ppm;
The absorption peak of other proton of maleopimaric acid and Si-CH
2-CH
2the absorption peak of-upper proton occurs within the scope of 0.5 ~ 3.0ppm continuously in a jumble;
Occur and proton O-CH on methoxyl group at 3.5ppm
3absorption peak.
Embodiment 2
Be terminal hydroxy group methyl silicone rubber (107 silicon rubber of 50PaS by 150 parts of viscosity, Chemicals company limited is held in Jinan ten thousand), gained modified resin MO-MPA-PDMS and 10 part of hydrophobic fumed R974 in 50 parts of embodiments 1, add in vacuum planetary mixer, at 80 DEG C, carry out dehydration blended 2 hours; After blended end, be cooled to room temperature, add 6 parts of methyltrimethoxy silanes and 0.3 part of dibutyl tin laurate, be uniformly mixed; Carry out packing under nitrogen protection.
Embodiment 3
According to the method shown in embodiment 2 and step, be distinguished as and the quality of the terminal hydroxy group methyl silicone rubber in formula and modified resin MO-MPA-PDMS is replaced by 120 parts and 80 parts respectively.
Embodiment 4
According to the method shown in embodiment 2 and step, be distinguished as and the quality of the terminal hydroxy group methyl silicone rubber in formula and modified resin MO-MPA-PDMS is replaced by 100 parts and 100 parts respectively.
Embodiment 5
According to the method shown in embodiment 2 and step, be distinguished as and the quality of the terminal hydroxy group methyl silicone rubber in formula and modified resin MO-MPA-PDMS is replaced by 50 parts and 150 parts respectively.
Embodiment 6
According to the method shown in embodiment 3 and step, be distinguished as and the methyltrimethoxy silane in formula is replaced by methyl tributanoximo silane.
Embodiment 7
According to the method shown in embodiment 3 and step, be distinguished as and the methyltrimethoxy silane in formula is replaced by vinyltriisopropenyloxysilane, dibutyl tin laurate is replaced by tetrabutyl titanate.
Comparative example 1
According to the method shown in embodiment 2 and step, be distinguished as and the quality of the terminal hydroxy group methyl silicone rubber in formula and modified resin MO-MPA-PDMS is replaced by 200 parts and 0 part respectively.
Comparative example 2
Add 100g octamethylcyclotetrasiloxane, 20g t etram-ethyltetravinylcyclotetrasiloxane, 34g amine hydroxypropyl methyl diethoxy silane, 10g hexamethyldisiloxane and 0.2g potassium hydroxide in a kettle., stirring reaction 8 hours at 100 DEG C, then be warming up to 180 DEG C gradually, vacuumize and remove low-boiling-point substance; Be cooled to 120 DEG C and add 72g maleopimaric acid (purity is 98%), stirring reaction is warming up to 180 DEG C and vacuumizes and remove low-boiling-point substance after 4 hours; Collect maleopimaric acid modified organic silicone resin MP-VMS while hot under nitrogen protection.
According to the method shown in embodiment 4 and step, be distinguished as and the MO-MPA-PDMS in formula is replaced by above-mentioned resin M P-VMS.
Performance test
Mechanical property characterizes: according to the principle shown in GB GBT 528-2009 and GBT531.1-2008 and method, and under 25 DEG C of conditions with relative humidity 50%, sulfuration is after 20 days, in the sensing chamber of fixed temperature and humidity, carry out Mechanics Performance Testing.
Stripping strength: according to the principle shown in GB GB-T2790-1995 and method, under 25 DEG C of conditions with relative humidity 50%, sulfuration is after 20 days, in the sensing chamber of fixed temperature and humidity, carry out Mechanics Performance Testing, observes bond failure state.
Above-mentioned each the performance test results sees the following form 1.
Table 1-1
Table 1-2
From upper table 1, along with the raising of methoxy group maleopimaric acid modification methyl silicone resins MO-MPA-PDMS consumption, stripping strength and the cohesive failure rate of room temperature vulcanization organosilicon rubber significantly improve, and hardness and tensile strength slightly improve, and elongation at break significantly improves.Applicant finds this after deliberation mainly owing to introducing maleopimaric acid and imide molecular structure in silicone molecules side chain, internal cohesive energy and the polarity of silicon rubber molecule are significantly improved, Intermolecular Forces significantly improves, finally cause the interfacial adhesion of sulphurated siliastic and the base material such as metal and plastics to improve, mechanical property (especially elongation at break) is also improved.
Claims (10)
1. a single-component high adhesion room temperature vulcanization organosilicon rubber, is characterized in that: its raw material comprises following component:
Hydroxy-terminated silicone rubbre: 50 ~ 150 parts;
Alkoxy end-capped maleopimaric acid modified polysiloxane resin: 50 ~ 150 parts;
Filler: 10 ~ 20 parts;
Linking agent: 2 ~ 10 parts;
Catalyzer: 0.1 ~ 0.5 part;
Above-mentioned number is mass fraction.
2. single-component high adhesion room temperature vulcanization organosilicon rubber as claimed in claim 1, is characterized in that: the structure of alkoxy end-capped maleopimaric acid modified polysiloxane resin is:
Wherein,
R
1for methoxy or ethoxy;
R
2and R
3for the straight-chain alkyl of carbon number 1 ~ 3;
The value of a is 0,1 or 2;
The span of m and n is 1 ~ 100, and meets simultaneously: 0.5≤n/ (m+n)≤0.02;
X to be carbon number be 2 ~ 10 alkylidene group, i.e.-C
bh
2b-1-, 10≤b≤2.
3. single-component high adhesion room temperature vulcanization organosilicon rubber as claimed in claim 1 or 2, is characterized in that: the range of viscosities of described hydroxy-terminated silicone rubbre is 10 ~ 100PaS.
4. single-component high adhesion room temperature vulcanization organosilicon rubber as claimed in claim 1 or 2, is characterized in that: described filler is vapor phase process or precipitated silica or through trimethyl silicane surface-treated thermal silica.
5. single-component high adhesion room temperature vulcanization organosilicon rubber as claimed in claim 1 or 2, is characterized in that: linking agent is the mixture of one or more any proportionings in dealcoholizing-type linking agent, de-oxime type linking agent or deacetone linking agent.
6. single-component high adhesion room temperature vulcanization organosilicon rubber as claimed in claim 5, is characterized in that: dealcoholizing-type linking agent is the mixture of one or more any proportionings in methyltrimethoxy silane, vinyltrimethoxy silane, methyl silicate, tetraethoxy or positive silicic acid propyl ester;
De-oxime type linking agent is the mixture of one or more any proportionings in methyl tributanoximo silane, vinyl tributyl ketoximyl silane or phenyl tributanoximo silane;
Deacetone linking agent is the mixture of any one or two kinds in methyl three iso-propenyloxysilane, vinyltriisopropenyloxysilane or phenyl three iso-propenyloxysilane and above any proportioning.
7. the single-component high adhesion room temperature vulcanization organosilicon rubber described in claim 1 or 2, is characterized in that: catalyzer is organic tin catalyzer or organic titanium class catalyzer.
8. single-component high adhesion room temperature vulcanization organosilicon rubber as claimed in claim 7, is characterized in that: organic tin catalyzer is the mixture of one or both and above proportioning arbitrarily in dibutyl tin dilaurate, dibutyl tin acetate, stannous octoate or stannous iso caprylate;
Organic titanium class catalyst Ti isopropyl propionate, tetrabutyl titanate or ethylacetoacetate titanium to boil together in thing the mixture of one or both and above proportioning arbitrarily.
9. the single-component high adhesion room temperature vulcanization organosilicon rubber described in claim 1 or 2, is characterized in that: the preparation method of alkoxy end-capped maleopimaric acid modified polysiloxane resin, comprises the following steps that order connects:
Step 1: by octamethylcyclotetrasiloxane D
4100 parts, containing primary amine groups-NH
2alkoxy silane coupling agent hydrolyzate 1 ~ 200 part, end-capping reagent organoalkoxysilane 2 ~ 100 parts and Tetramethylammonium hydroxide mixing, insulation reaction is stirred 4 ± 0.2 hours at 100 ± 5 DEG C, wherein, the quality of Tetramethylammonium hydroxide accounts for reactant total mass 0.1%, and described number is mass fraction;
Step 2: add maleopimaric acid powder in the material of step 1 products therefrom, and be warming up to 150 ± 5 DEG C gradually in 4 ± 0.2 hours, reaction terminates, wherein, maleopimaric acid with containing primary amine groups-NH
2alkoxy silane coupling agent hydrolyzate mole dosage equal;
Step 3: after step 2 reaction terminates, reaction system is warming up to 180 ± 5 DEG C gradually, and vacuum takes off low-boiling-point substance 2 ± 0.2 hours, and the state of obtaining is the alkoxy end-capped maleopimaric acid modified polysiloxane resin of light brown homogeneous phase transparent thick liquid.
10. the preparation method of the single-component high adhesion room temperature vulcanization organosilicon rubber described in claim 1-9 any one, is characterized in that: comprise the following steps that order connects:
A, hydroxy-terminated silicone rubbre, alkoxy end-capped maleopimaric acid modified polysiloxane resin and filler added in vacuum planetary mixer and in the temperature range of 50 ~ 100 DEG C, carries out dehydration blended 1 ~ 4 hour;
After B, blended end, be cooled to room temperature, add linking agent and catalyzer, be uniformly mixed;
C, carry out packing under nitrogen protection.
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| CN105062078A (en) * | 2015-09-09 | 2015-11-18 | 蓝星（成都）新材料有限公司 | Silicon rubber for room-temperature quick-curing potting and preparation method thereof |
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| CN104045834B (en) * | 2014-06-25 | 2017-03-15 | 中国林业科学研究院林产化学工业研究所 | A kind of maleopimaric acid modified polysiloxane resin and preparation method thereof |
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| CN105062078A (en) * | 2015-09-09 | 2015-11-18 | 蓝星（成都）新材料有限公司 | Silicon rubber for room-temperature quick-curing potting and preparation method thereof |
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